Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H11NO3.ClH |
Molecular Weight | 181.617 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC(=O)CCC(=O)CN
InChI
InChIKey=UJYSYPVQHFNBML-UHFFFAOYSA-N
InChI=1S/C6H11NO3.ClH/c1-10-6(9)3-2-5(8)4-7;/h2-4,7H2,1H3;1H
DescriptionSources: http://www.drugbank.ca/drugs/DB00992Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021415s004lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00992
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021415s004lbl.pdf
Methyl aminolevulinate is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy. Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Methyl aminolevulinate is used for topical use, in combination with 570 to 670 nm wavelength red light illumination, in the treatment of non-hyperkeratotic actinic keratoses of the face and scalp in immunocompetent patients when used in conjunction with lesion preparation (debridement using a sharp dermal curette).
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map00860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25048871 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | METVIXIA Approved UseMETVIXIA Cream in combination with Aktilite CL128 lamp red light illumination is indicated for treatment of thin and moderately thick, non-hyperkeratotic, non-pigmented actinic keratoses of the face and scalp in immunocompetent patients. This photodynamic therapy should be used in conjunction with appropriate lesion preparation in the physician’s office when other therapies are considered medically less appropriate. Launch Date2004 |
Doses
Dose | Population | Adverse events |
---|---|---|
1 g single, topical Dose: 1 g Route: topical Route: single Dose: 1 g Sources: |
unhealthy, adult n = 383 Health Status: unhealthy Condition: actinic keratosis Age Group: adult Population Size: 383 Sources: |
Disc. AE: Pain localised... AEs leading to discontinuation/dose reduction: Pain localised (1%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Pain localised | 1% Disc. AE |
1 g single, topical Dose: 1 g Route: topical Route: single Dose: 1 g Sources: |
unhealthy, adult n = 383 Health Status: unhealthy Condition: actinic keratosis Age Group: adult Population Size: 383 Sources: |
PubMed
Title | Date | PubMed |
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The role of light in the treatment of non-melanoma skin cancer using methyl aminolevulinate. | 2003 |
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[In actinic keratosis and basal cell carcinoma. The power of light heals without scars]. | 2003 Mar 27 |
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Effectiveness of different light sources for 5-aminolevulinic acid photodynamic therapy. | 2004 |
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[Photodynamic therapy of cutaneous leishmaniasis. A promising new therapeutic modality]. | 2004 Apr |
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Photodynamic therapy for subungual Bowen's disease. | 2004 Aug |
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[Photodynamic therapy with methylaminooxopentanoate (Metvix) and a broad band light source (PhotoDyn 501): practical experiences in problem-patients with actinic keratoses and basal cell carcinomas]. | 2004 Dec |
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Allergic contact dermatitis to 5-aminolaevulinic acid methylester but not to 5-aminolaevulinic acid after photodynamic therapy. | 2004 Jan |
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Photodynamic therapy using topical methyl aminolevulinate vs surgery for nodular basal cell carcinoma: results of a multicenter randomized prospective trial. | 2004 Jan |
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Iontophoretic delivery of 5-aminolevulinic acid and its methyl ester using a carbopol gel as vehicle. | 2004 Jul 23 |
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Gateways to clinical trials. | 2004 Jul-Aug |
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Photodynamic therapy with topical methyl aminolaevulinate for 'difficult-to-treat' basal cell carcinoma. | 2005 Apr |
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Methyl aminolaevulinate photodynamic therapy for Bowen's disease: a practical option? | 2005 Feb |
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Methyl aminolaevulinate photodynamic therapy in practice: treatment protocol. | 2005 Feb |
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Practical aspects of methyl aminolaevulinate photodynamic therapy. | 2005 Feb |
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Topical photodynamic therapy for Bowen's disease. | 2005 Feb |
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Clinical efficacy of methyl aminolaevulinate photodynamic therapy in basal cell carcinoma and solar keratosis. | 2005 Feb |
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Pain, pain relief and other practical issues in photodynamic therapy. | 2005 Feb |
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Photodynamic therapy. | 2005 Feb |
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Gateways to clinical trials. | 2005 Jul-Aug |
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Gateways to clinical trials. | 2005 Jun |
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Kinetics of protoporphyrin IX formation in rat oral mucosa and skin after application of 5-aminolevulinic acid and its methylester. | 2005 Mar-Apr |
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Gateways to clinical trials. | 2005 May |
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Influence of light exposure on the kinetics of protoporphyrin IX formation in normal skin of hairless mice after application of 5-aminolevulinic acid methyl ester. | 2005 Nov |
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Morphine gel 0.3% does not relieve pain during topical photodynamic therapy: a randomized, double-blind, placebo-controlled study. | 2006 |
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Successful treatment of disseminated superficial actinic porokeratosis with methyl aminolevulinate-photodynamic therapy. | 2006 |
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Fluorescence diagnosis and photodynamic therapy in dermatology from experimental state to clinic standard methods. | 2006 |
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Photodynamic therapy induces less pain in patients treated with methyl aminolevulinate compared to aminolevulinic acid. | 2006 Apr |
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Photodynamic therapy of acne vulgaris using 5-aminolevulinic acid versus methyl aminolevulinate. | 2006 Apr |
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Multiple large surface photodynamic therapy sessions with topical methylaminolaevulinate in PTCH heterozygous mice. | 2006 Apr |
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Topical photodynamic therapy: an introduction for nurses. | 2006 Aug 10-Sep 13 |
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Successful treatment of necrobiosis lipoidica diabeticorum with photodynamic therapy. | 2006 Dec |
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Gateways to clinical trials. | 2006 Jun |
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A case of focal dermal hypoplasia (Goltz) syndrome with exophytic granulation tissue treated by curettage and photodynamic therapy. | 2006 Mar |
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Gateways to clinical trials. | 2006 May |
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[Dynamic phototherapy in dermatology: current uses and future perspectives]. | 2006 May |
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Gateways to clinical trials. | 2006 Oct |
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Topical application of 5-aminolaevulinic acid, methyl 5-aminolaevulinate and hexyl 5-aminolaevulinate on normal human skin. | 2006 Oct |
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A study comparing endogenous protoporphyrin IX induced by 5-ALA and ALA-methyl ester with exogenous PpIX and PpIX dimethyl ester in photodynamic diagnosis of human nasopharyngeal carcinoma xenografts. | 2006 Oct |
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Photodynamic therapy with methylaminolevulinate as a valuable treatment option for unilesional cutaneous T-cell lymphoma. | 2006 Oct |
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Topical methyl aminolevulinate photodynamic therapy for the treatment of folliculitis. | 2007 Aug |
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Allergic contact dermatitis to methyl aminolevulinate (Metvix) cream used in photodynamic therapy. | 2007 Feb |
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Phototoxic reaction and porphyrin fluorescence in skin after topical application of methyl aminolaevulinate. | 2007 Feb |
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A comparative study of intense pulsed light alone and its combination with photodynamic therapy for the treatment of facial acne in Asian skin. | 2007 Jan |
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Chemopreventative thoughts for photodynamic therapy. | 2007 Jan |
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Identification of tetrapyrrole compounds excreted by Rhodobacter sphaeroides and sources of the methyl hydrogens of bacteriochlorophyll a biosynthesized by R. sphaeroides, based on 13C-NMR spectral analysis of coproporphyrin III tetramethyl ester. | 2007 Jul |
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The efficacy of photodynamic therapy in actinic cheilitis of the lower lip: a prospective study of 15 patients. | 2007 Jul |
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Randomized, double-blind, prospective study to compare topical 5-aminolaevulinic acid methylester with topical 5-aminolaevulinic acid photodynamic therapy for extensive scalp actinic keratosis. | 2007 Jul |
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Photodetection of basal cell carcinoma using methyl 5-aminolaevulinate-induced protoporphyrin IX based on fluorescence image analysis. | 2007 Jul |
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Fluorescence diagnosis of face-located basal cell carcinomas: a new dermatological procedure which may help the surgeon. | 2007 Mar-Apr |
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Photodynamic therapy for cutaneous verrucous carcinoma. | 2007 Sep |
Patents
Sample Use Guides
Using a spatula, apply a layer of METVIXIA Cream (Methyl aminolevulinate) about 1 mm thick to the lesion and the surrounding 5 mm of normal skin. Do not apply more than one gram (half tube) of METVIXIA Cream per treatment session.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25048871
0.5-2mM Methyl aminolevulinate induced formation of porphyrin in malignant cells (HS192T) and human FLS from RA and OA patients.
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C1420
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ACTIVE MOIETY
SUBSTANCE RECORD